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Volumn 40, Issue 50, 1999, Pages 8873-8876

Stereocontrol in the reduction of meso-imides using oxazaborolidine, leading to a facile synthesis of (+)-deoxybiotin

Author keywords

(+) deoxybiotin; L threonine; Meso imide; Oxazaborolidine

Indexed keywords

BIOTIN DERIVATIVE; BORANE DERIVATIVE; IMIDE; LACTAM; THREONINE;

EID: 0033544749     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01864-X     Document Type: Article
Times cited : (31)

References (22)
  • 1
    • 0002032726 scopus 로고
    • For reviews, see: (a) Whitesell, J. K. Chem. Rev. 1989, 89, 1581-1590.
    • (1989) Chem. Rev. , vol.89 , pp. 1581-1590
    • Whitesell, J.K.1
  • 3
    • 85037512423 scopus 로고
    • and references cited therein
    • (c) Harada, T.; Oku, A. Synlett 1994, 95-104 and references cited therein.
    • (1994) Synlett , pp. 95-104
    • Harada, T.1    Oku, A.2
  • 11
    • 0001516297 scopus 로고    scopus 로고
    • and references cited therein
    • For the synthesis of biotin, see: (a) De Clercq, P. J. Chem. Rev. 1997, 97, 1755-1792 and references cited therein,
    • (1997) J. Chem. Rev. , vol.97 , pp. 1755-1792
    • De Clercq, P.1
  • 16
    • 85038138082 scopus 로고    scopus 로고
    • note
    • 3·THF complex (1.56 mL, 1.56 mmol) in THF was added during 2 h at 0°C. After stirring for 20 h at rt, the reaction mixture was quenched by adding a phosphate buffer (10 mL), and the repeated extraction with ethyl acetate followed by usual work-up gave a crude oil, which was purified on preparative TLC (eluent: n-Hex:AcOEt 2:1) to give the hydroxy lactam 3d as a white powder (215.0 mg, 65%).
  • 19
    • 85038143920 scopus 로고    scopus 로고
    • note
    • 6b
  • 20
    • 0016365579 scopus 로고
    • Ogino, S.; Fujimoto, S.; Aoki, Y. Agric. Biol. Chem. 1974, 38, 275-277. Aoki, Y.; Suzuki, H.; Akiyama, H.; Okano, S.Japan Kokai 1974, 7487691; Chem. Abstr. 1975, 82, 156300b.
    • (1974) Agric. Biol. Chem. , vol.38 , pp. 275-277
    • Ogino, S.1    Fujimoto, S.2    Aoki, Y.3
  • 21
    • 84996309380 scopus 로고
    • Ogino, S.; Fujimoto, S.; Aoki, Y. Agric. Biol. Chem. 1974, 38, 275-277. Aoki, Y.; Suzuki, H.; Akiyama, H.; Okano, S. Japan Kokai 1974, 7487691; Chem. Abstr. 1975, 82, 156300b.
    • (1974) Japan Kokai , pp. 7487691
    • Aoki, Y.1    Suzuki, H.2    Akiyama, H.3    Okano, S.4
  • 22
    • 84996309380 scopus 로고
    • Ogino, S.; Fujimoto, S.; Aoki, Y. Agric. Biol. Chem. 1974, 38, 275-277. Aoki, Y.; Suzuki, H.; Akiyama, H.; Okano, S.Japan Kokai 1974, 7487691; Chem. Abstr. 1975, 82, 156300b.
    • (1975) Chem. Abstr. , vol.82


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.